WO2019227382A1 - 具有抗病毒效果的绿豆皮萃取物及其萃取方法 - Google Patents

具有抗病毒效果的绿豆皮萃取物及其萃取方法 Download PDF

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WO2019227382A1
WO2019227382A1 PCT/CN2018/089229 CN2018089229W WO2019227382A1 WO 2019227382 A1 WO2019227382 A1 WO 2019227382A1 CN 2018089229 W CN2018089229 W CN 2018089229W WO 2019227382 A1 WO2019227382 A1 WO 2019227382A1
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mung bean
alcohol extract
alcohol
pharmaceutical composition
composition according
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PCT/CN2018/089229
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English (en)
French (fr)
Chinese (zh)
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陈慧文
尤封陵
洪宜年
毕家甄
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京冠生物科技股份有限公司
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Priority to JP2021517086A priority Critical patent/JP7271818B2/ja
Priority to US17/058,432 priority patent/US20210196777A1/en
Priority to PCT/CN2018/089229 priority patent/WO2019227382A1/zh
Publication of WO2019227382A1 publication Critical patent/WO2019227382A1/zh

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/31—Extraction of the material involving untreated material, e.g. fruit juice or sap obtained from fresh plants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/50—Methods involving additional extraction steps
    • A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying

Definitions

  • the invention relates to a medicinal composition of mung bean skin extract and an extraction method thereof, in particular to a medicinal composition of mung bean skin extract having an antiviral effect, an extraction method and application thereof.
  • mung beans are mainly used to relieve swelling and lower qi, clear heat and detoxify, treat erysipelas, diuretic and thirst, thicken the stomach, make pillows and eyesight, cure head wind, headache, tonic energy, reconcile the five internal organs, calm the mind, and perform the work
  • the two meridians moisturize the skin, and relieve all the poisonous poisons.
  • Mung beans are sweet, cold, and non-toxic. They have the effects of clearing away heat and diminishing heat, diuretic and swelling, soothing throat and thirst, and lowering blood pressure. They have good curative effects on heat stroke and pharyngitis, so they are commonly used as folk holy products.
  • Mung beans, tofu and bean sprouts all have different functions. Mung beans can reduce swelling and ventilation, clear heat and detoxify, intestines and stomach, treat colds and headaches, often eat tonic energy, reconcile the five internal organs, and pass through the twelve meridians. Mung bean skin Gan Han is non-toxic, can relieve fever, and treat headache and headache. Mung bean sprouts Ganping, hangover and antipyretics, and benefit Sanjiao. Mung bean pods can cure long-term blood pupa. Modern research has confirmed that mung bean has a high nutritional value, contains more protein than rice, is rich in carbohydrates, has less fat, and contains protein, calcium, phosphorus, iron, and carotene. Drinking mung bean soup often in summer can prevent various sores caused by heat stroke and heat poisoning, and it is helpful to nephritis, diabetes, hypertension, arteriosclerosis, gastroenteritis, and laryngitis.
  • Mung beans contain about 20 to 24% protein, mainly globulin and albumin, which are the main types of storage proteins. Because mung bean contains high protein content and is rich in many essential amino acids, it is relatively deficient in threonine, sulfur-containing amino acids, lysine, and tryptophan, and is suitable for digestion of economic animals. The rate is poor and difficult to apply to economic animals (Randhir and Shetty, 2007). However, little research has been done on the nutritional content of mung bean skin.
  • a virus is an organism that is smaller than a bacterium and needs to be seen with an electron microscope. At present, medicine has not yet found a very effective antiviral agent. It mainly needs the immunity of the human or animal body to fight the virus infection. Common viral infections include enterovirus, HIV, hepatitis virus, polio, influenza, upper respiratory tract infection, etc., and their ability to spread is often prone to epidemics. Among them, influenza (referred to as influenza), whether in humans or animals, influenza viruses cause huge public health safety hazards and economic losses, and solutions are urgently sought.
  • the invention relates to an antiviral pharmaceutical composition, which is obtained by first extracting mung bean skin raw materials, and then immersing and extracting them with 5 to 15 times (v / w) C1 to C6 alcohols by ultrasonic soaking, and then concentrating and drying the obtained product. mixture.
  • the source of the mung bean skin raw material of the present invention is a trade name (Beijing Crown) or ( ⁇ ⁇ ) or a combination thereof.
  • the alcohol extraction step used in the present invention uses 50%, 75%, 95% alcohol or methanol, and its extraction volume is 10 times the volume of the raw material (v / w).
  • the alcohol extraction method of the present invention uses ultrasonic vibration. After one hour of shaking extraction at room temperature, the residue solids are removed to obtain a mung bean alcohol extract.
  • the mung bean alcohol extract of the present invention is dried at 50-60 ° C. to obtain a mung bean alcohol extract.
  • the mung bean alcohol extract of the present invention contains about 2 to 7% vitexin or 2 to 7% isovitexin or a combination thereof.
  • the mung bean extract of the present invention can inhibit the cytopathic effect caused by viruses, and these viruses preferably include orthomyxoviridae (such as influenza virus, avian influenza virus), and paramyxoviridae (such as Newtown virus). , Herpes virus, or reovirus.
  • viruses preferably include orthomyxoviridae (such as influenza virus, avian influenza virus), and paramyxoviridae (such as Newtown virus). , Herpes virus, or reovirus.
  • the mung bean extract of the present invention can reduce the hemagglutination assay (HA) power of the virus to red blood cells.
  • viruses preferably include the family Orthomyxoviridae (such as influenza virus, avian influenza virus), parasite Myxoviridae (such as Newcastle virus), herpes virus, or reovirus.
  • the mung bean alcohol extract of the present invention achieves an antiviral effect by inhibiting ⁇ -glucosidase.
  • the mung bean extract of the present invention achieves an antiviral effect by inhibiting neuraminidase.
  • viruses preferably include orthomyxoviridae (such as influenza virus, avian influenza virus), paramyxoviridae (such as Newtown Virus), herpes virus, or reovirus.
  • viruses inhibited by the mung bean extract of the present invention include orthomyxoviridae (such as influenza virus, avian influenza virus), paramyxoviridae (such as Newcastle virus), herpes virus, or reovirus ).
  • orthomyxoviridae such as influenza virus, avian influenza virus
  • paramyxoviridae such as Newcastle virus
  • herpes virus or reovirus
  • the present invention also relates to a method for extracting a pharmaceutical composition of an antiviral mung bean skin extract, comprising: (1) providing a raw material of mung bean skin; (2) a C1 to C6 alcohol at 5 to 15 times (v / w) Extract the aforementioned mung bean skin raw materials for extraction to obtain a soaking solution; (3) filter the soaking solution to obtain an alcohol extract and concentrate and dry it; and (4) obtain a mung bean skin alcohol extract.
  • the source of the mung bean skin raw material of the present invention is a trade name or Or a combination thereof.
  • the alcohol extraction step of the present invention uses 50%, 75%, 95% alcohol or methanol, and the extraction volume is 10 times the volume of the raw material (v / w).
  • the alcohol extraction method of the present invention uses ultrasonic vibration. After one hour of shaking extraction at room temperature, the residue solids are removed to obtain a mung bean alcohol extract.
  • the mung bean alcohol extract of the present invention is dried at 50-60 ° C. to obtain a mung bean alcohol extract.
  • the invention also relates to a feed additive prepared by the aforementioned extraction method.
  • 1a to 1d are normal distribution diagrams of vitexin and isovitexin after being extracted by the method of the present invention.
  • Figure 2 shows the standard product 25 ppm Vitexin, 25 ppm Isovitexin, Methanol and Chromatogram of ethanol extract.
  • FIG. 3 is a schematic diagram of an extraction process according to the present invention.
  • FIG. 4 is a HPLC column chromatogram of the extract of the present invention.
  • FIG. 5 is a cytotoxicity test result of the mung bean skin alcohol extract of the present invention.
  • FIG. 6 is a test result of cytopathic effect of alcohol extract of mung bean skin according to the present invention.
  • FIG. 7 is a result of a virus HA titer test for reducing the cell performance of a viral extract of mung bean skin according to the present invention.
  • FIG. 8 is a test result of the ability of the mung bean skin alcohol extract to inhibit alpha-glucosidase.
  • Figures 9a-9d show the results of the ability of the mung bean skin alcohol extract to inhibit neuraminidase.
  • the invention relates to a mung bean skin extract which can be used as an antiviral effect.
  • the extract is processed by Jingguan Biotechnology, it is made into a trade name or Products, please refer to Figure 1a to Figure 1d.
  • Normal distribution curve analysis of mung bean skin from different batches and origins can obtain high content of vitexin and isovitexin mixture, please refer to Figure 2 , which is the standard 25ppm Vitexin, 25ppm Isovitexin, Methanol and
  • the chromatogram of the ethanol extract can be found that the extraction method of the present invention can overcome the changes caused by factors such as the environment and climate of the place of origin of natural products, so that the active ingredients can be qualitative and quantitative, so as to achieve a stable quality effect, and Can be applied to animal feed additives or food additives. Therefore, the present invention also relates to a feed additive for promoting animal health.
  • the present invention relates to a mung bean skin extract having a cytopathic effect of reducing viruses and reducing HA force value.
  • viruses preferably include orthomyxoviridae (such as influenza virus, avian influenza virus), paramyxoviridae (such as Newcastle virus), herpes virus or reovirus, wherein via the extraction method disclosed in the present invention and its extract, the extract mainly contains vitexin and isovitexin, two active ingredients It has the ability to inhibit alpha-glucosidase enzymes and neuraminidase, thereby achieving antiviral effects.
  • the mung bean skin extract of the present invention can preferably be extracted with alcohols from C1 to C6, but is not limited to using 50%, 75%, 95% alcohol, methanol or other alcohols, and it is preferable to use alcohol extraction, and different concentrations of Alcohol extraction results contained a certain amount of vitexin and isovitexin.
  • alcohol extracts or wine extracts are referred to as alcohol extracts or wine extracts.
  • Example 1 Extraction of active ingredients from mung bean skin extract
  • FIG 3 Take the mung bean skin raw materials, and use Jingguan Biotech's manufacturing process, after the production schedule, raw material mixing, physical chemistry and biological treatment, and then measure and package to obtain the finished product.
  • the product name is or Can be used as animal feed additives or other food additives.
  • a small amount of extraction was performed in the laboratory using a weight unit of 50 g. 50 g of the animal feed supplement is added to 10 times the volume (500 ml) of 95% alcohol, which is extracted by ultrasonic method, and shaken at room temperature for one hour, and the residual solids are removed by coarse filtration to obtain the mung bean skin alcohol extract of the present invention At this time, the volume is about 350-380ml, and the recovery amount is about 70-80%.
  • Example two active ingredient test of mung bean skin alcohol extract
  • the mung bean skin alcohol extract obtained in Example 1 was dissolved in DMSO, 1.4 g of the mung bean skin alcohol extract was dissolved in 14 ml of DMSO, and then diluted 100-fold with methanol, and the composition was initially analyzed by HPLC. Please refer to FIG. 4. After comparing the standards, it is confirmed that the two peaks generated between the residence time of about 25-30 minutes are vitexin and isovitexin respectively. According to the actual calculation of the absolute amount, vitexin was 31.015 mg (2.22% of the alcohol extract), and isovitexin was 33.893 mg (2.42% of the alcohol extract).
  • vitexin and isovitexin have the ability to inhibit alpha-glucosidase, and also have the effect of inhibiting neuraminidase To achieve the ability to inhibit viral activity.
  • the pure substances or standards of vitexin and isovitexin are very expensive. The amount of 10mg depends on its purity. The market price is as high as NT $ thousands to tens of thousands of yuan. Among them, isovitexin is more expensive. However, it is limited by the price, making it practically not applicable in the industry, and there are limitations on the application level.
  • the present invention further tests the cytotoxicity test of the alcohol extract.
  • the blank control group is DMSO. Under 1% DMSO concentration, the cell's There is no difference in growth pattern and there is no toxicity.
  • the cell line used is MDCK cells (dog kidney epithelial cells). MDCK is a cell line commonly used in the flu test.
  • the cell culture medium used is DMEM, and 10% FBS serum and 1% PSA triple antibiotics are added. 5.6ml DMSO was used to dissolve 1.4g mung bean skin alcohol extract to become a high concentration 250mg / ml mung bean skin alcohol extract preservation solution, and then diluted with DMSO to a concentration of 62.5, 125, 250, 500, 1000, 2000 ( ⁇ g / ml) ). Cells were seeded in a petri dish, and the cells were allowed to grow for 24 hours.
  • the mung bean skin alcohol extract to be tested was added, and then cell survival analysis (MTT assay) was performed at 24, 48, and 72 hours, respectively.
  • MTT assay cell survival analysis
  • Example 4 Antiviral test-Alcohol extract of mung bean skin inhibits cytopathic effects of influenza virus (Cytopathic effect, CPE)
  • Influenza virus particles will kill host cells and cause cytopathic effects (CPE) after infecting cells. Therefore, if they can inhibit cytopathic effects, they can also be regarded as having antiviral effects.
  • CPE cytopathic effects
  • MDCK cells dog kidney epithelial cells
  • the virus strain is PR8 (H1N1).
  • the concentration of alcohol extract of mung bean skin used is 0,125,2000 ( ⁇ g / ml), and 0 ⁇ g / ml is a DMSO blank control group.
  • the method is to inoculate the cell line first, and after 24 hours, pretreat the mung bean skin alcohol extract and MDCK cells with different concentrations for 1 hour, and pretreat the mung bean skin alcohol extract and PR8 virus strain with different concentrations for 1 hour, and then The virus pretreated with the alcohol extract of mung bean skin and the cell line pretreated with the alcohol extract of mung bean skin were co-cultured for infection. The virus solution was removed after 1 hour of infection and the alcohol extract of mung bean skin was added. After 24 hours, Observe the results of the CPE test.
  • the use of the mung bean skin alcohol extract of the present invention can reduce the occurrence of cytopathic effect, and no cytopathic effect is seen at a concentration of 2000 ⁇ g / ml , And the appearance of cells under a microscope was normal.
  • Example 5 Antiviral Test-Alcohol Extract of Mung Bean Skin Reduces Influenza Virus HA of Cells
  • Hemagglutinin on the surface of the influenza virus can bind to the receptor of red blood cells. When the virus power is high enough, hemagglutination will occur in the red blood cells. Therefore, analysis of the agglutination of red blood cells can be used as a method for testing the power of viruses. This is also called hemagglutination assay (HA).
  • HA hemagglutination assay
  • the cell line used in the test and the mung bean skin alcohol extract of the present invention had the same concentration as in Example 4.
  • the method is to inoculate the cell line first, and after 24 hours, pretreat the mung bean skin alcohol extract and MDCK cells with different concentrations for 1 hour, and pretreat the mung bean skin alcohol extract and PR8 virus strain with different concentrations for 1 hour, and then
  • the virus pretreated with the alcohol extract of mung bean skin and the cell line pretreated with the alcohol extract of mung bean skin were co-cultured for infection.
  • the virus was removed after 1 hour of infection and the alcohol extract of mung bean skin was added.
  • the cell culture fluid was collected and subjected to a HA titer test.
  • the results of FIG. 7 show that the mung bean skin alcohol extract of the present invention cannot detect the HA titer produced by the cells at 2000 ⁇ g / ml. Therefore, it can be seen that the mung bean skin alcohol extract of the present invention can reduce the HA titer of influenza virus produced in MDCK cells. .
  • the virus species may be a virus family that also requires ⁇ -glucosidase, such as orthomyxoviridae (such as influenza virus, avian influenza virus), paramyxoviridae (such as Newcastle virus), herpes virus, or Rio virus (reovirus), etc.
  • orthomyxoviridae such as influenza virus, avian influenza virus
  • paramyxoviridae such as Newcastle virus
  • herpes virus or Rio virus (reovirus)
  • neuraminidase is an influenza virus that releases indispensable enzymes from host cells, it is also a strategy to inhibit neuraminidase activity for the treatment of influenza. In fact, influenza has also been treated clinically via neuraminidase inhibitors.
  • a neuraminidase obtained from mammalian influenza virus H1N1 (PR8) and avian influenza virus H6N1 (3937) to perform a neuraminidase activity inhibition test of the mung bean skin alcohol extract of the present invention .
  • the mung bean skin alcohol extract has a dose-dependent effect on the neuraminidase inhibitory ability, whether for mammalian influenza virus or avian influenza virus. .
  • This result indicates that the mung bean skin alcohol extract of the present invention has excellent ability to inhibit neuraminidase activity, and thus can exhibit antiviral ability and potential.
  • the virus species may be a mammalian influenza virus or an avian influenza virus.
  • the examples of the present invention show that the mung bean skin alcohol extract of the present invention has antiviral ability, and its mechanism may be to achieve antiviral effect by inhibiting viral ⁇ -glucosidase and neuraminidase, so it can be applied It is used for combating virus species with ⁇ -glucosidase and neuraminidase or with one of the enzymes.
  • the mung bean skin alcohol extract of the present invention has no cytotoxicity in vitro tests and is an excellent anti-virus product .
  • the extraction method and the obtained extract provided by the present invention have low raw material source cost, and the obtained vitexin and isovitexin or a combination thereof has high yield, good recovery rate, simple extraction method, and excellent
  • the cost advantage is conducive to industrial applications and has great value for development and protection.

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PCT/CN2018/089229 2018-05-31 2018-05-31 具有抗病毒效果的绿豆皮萃取物及其萃取方法 WO2019227382A1 (zh)

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Application Number Priority Date Filing Date Title
JP2021517086A JP7271818B2 (ja) 2018-05-31 2018-05-31 抗ウイルス作用を有するリョクトウ外皮抽出物及びその抽出方法
US17/058,432 US20210196777A1 (en) 2018-05-31 2018-05-31 Mung bean hull extract with antiviral effect and extraction method thereof
PCT/CN2018/089229 WO2019227382A1 (zh) 2018-05-31 2018-05-31 具有抗病毒效果的绿豆皮萃取物及其萃取方法

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Citations (2)

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CN101642484A (zh) * 2009-09-03 2010-02-10 咀香园健康食品（中山）有限公司 绿豆皮中黄酮类化合物的提取方法
CN101879208A (zh) * 2010-04-27 2010-11-10 南京泽朗农业发展有限公司 一种从绿豆壳中提取总黄酮的方法

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JP2015182990A (ja) 2014-03-26 2015-10-22 不二製油株式会社 抗糖化機能を有する食品添加用組成物及び抗糖化剤

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CN101642484A (zh) * 2009-09-03 2010-02-10 咀香园健康食品（中山）有限公司 绿豆皮中黄酮类化合物的提取方法
CN101879208A (zh) * 2010-04-27 2010-11-10 南京泽朗农业发展有限公司 一种从绿豆壳中提取总黄酮的方法

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LI XIA ET AL.: "Optimization of Ultrasonic- Assisted Enzymatic Extraction of Flavonoids from Mung Bean Coat", FOOD SCIENCE, vol. 38, no. 8, 15 August 2017 (2017-08-15), pages 206 - 208 *
YAN JUAN ET AL.: "Research Progress of Pharmacological Action of Vitexin", SHANDONG MEDICAL JOURNAL, vol. 57, no. 17, 7 May 2017 (2017-05-07), pages 110 *
ZHANG YAN ET AL.: "Extraction Conditions for Flavonoids from Mung Bean Coat", JOURNAL OF THE CHINESE CEREALS AND OILS ASSOCIATION, vol. 24, no. 10, 25 October 2009 (2009-10-25), pages 124 - 125 *

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